CEO Corner: The co-CEO advantage

The longer you run a successful business, the easier it becomes to mistake familiarity for certainty.

You know every decision. Every scar. Every reason the company operates the way it does. That history creates judgment and pattern recognition. It also creates attachment.

You defend a process because you remember the problem it solved. You protect a structure because you helped build it. Eventually, experience can make it harder to question your own assumptions. You start holding the fixes in your own head and mask fundamental system gaps that will prevent the team and business from reaching its full potential.

One of the most valuable parts of sharing the CEO role for more than two decades has been having someone I trust enough to challenge mine.

My co-founder is the smartest person I have ever worked with (literally genius and math wizard). He also has total integrity, and we share the same commitment to the company we started more than 20 years ago. I trust his judgment and intentions, even when we see a decision differently. That confidence has given us the freedom to periodically do something most leaders find difficult: hand each other the teams we have built and invite the other person to make them better. We invite role changes and allow the fresh ideas, first principles thinking and new perspective to find ways to make all parts of our business better.

Have you ever moved and gone back to see your old house or apartment and be blown away by what the new owner did with the place? Many times, those ideas are in there but a fresh perspective or new energy is what it takes to break ahead into new patterns. Sometimes that’s the benefit of adding new talent or the role private equity investors can (sometimes) apply.

As co-CEOs, we divide responsibility for different areas of the company, giving each of us clear ownership. But those areas are not permanent territories. At important moments, we rotate.

Not because someone failed.

Because sometimes a business needs a leader who knows everything about it. And sometimes it needs a leader who does not and who will challenge assumptions and look for new ways to grow and transform to even higher levels.

Fresh eyes change the questions

We have made major rotations roughly half a dozen times since founding Achieve in 2002.

That is not frequent. It should not be. Rotate too often and you create chaos. Never rotate and you risk creating kingdoms and calcified practices or routines.

We make a change when an area of the company needs a different kind of leadership. Sometimes it needs a builder and disruptor. Sometimes it needs greater structure or stronger execution. Sometimes it simply needs someone who will walk into the room and simply ask: 

Why do we do it this way?

What would we build if we were starting today?

Are we protecting this because it works or because it is ours?

If we were fired, and a new CEO was hired in our shoes, what would they do differently?

Recently, I stepped into deeper responsibility for our lending business, an area I had never directly led or had meaningful involvement in. Suddenly, I was going deep on capital markets, securitization, pricing, credit and partnerships. Digital conversion, ABS issuance, channel expansion and product strategies.

I felt the first day founder energy again. New language. New ideas. New problems to solve. And… an awesome team full of ideas and leaders willing to be challenged and to grow together.

At the same time, my co-founder stepped into areas he hasn’t led in a decade or more. That required each of us to say: Look at what’s built. Find the weak spots I may have been protecting. Challenge the assumptions I no longer notice. Make it better. No ego. Just the first day commitment to building something great.

That is uncomfortable.

It is also one of the strongest things a leader can do.

The goal is not to protect your territory or prove whose approach is better. It is to build the best company possible for customers, teammates and shareholders.

Shared leadership requires clear ownership and deep trust

Two CEOs involved in every operational decision do not create twice the leadership. They create half the speed.

We divide responsibilities clearly. The person overseeing an area has the autonomy and room to lead it. We come together on decisions that could fundamentally change the company (and are collaborative with our entire top senior leadership team on major decisions), but we do not sit side by side debating every move.

If two co-CEOs agree on everything, one is probably redundant.

If they debate everything, both become a bottleneck.

When we need to make a decision together, we listen to each other, test the thinking challenging each other and then getting to the best decision and execution framework for success. In the instances (and they do exist) where we passionately debate an important decision, I like to put a percentage on how strongly we favor each option. I might be 60% in favor of one path while my co-founder is 80% in favor of another. We try to listen, learn, embrace constructive conflict but then get to an actual decision. Comparing those levels of conviction gives us more useful information than a simple yes or no.

If one of us has greater conviction, the other can trust that judgment and commit to the direction. For decisions that could existentially change the company, we keep working until we reach agreement. But not every decision requires equal conviction from both of us. We’re big on creating clear decision frameworks and knowing who and on what principles important decisions are made. It removes unnecessary friction and it helps build trust and alignment.

Once we choose, we go.

No “I told you so.” No waiting to see who was right. We walk through the door together and focus on how to win now that a decision has been made. That could mean I am going to “disagree and commit” but there will be commitment to success no matter what an original opinion was. Having a sounding board to challenge your ideas and someone who you want to impress and to rise to their level has always brought a level of rigor and maturity to how we lead our company as co-CEOs.

Sometimes trust means leading with conviction. Sometimes it means recognizing that your partner sees something more clearly and following with the same level of commitment. We have our moments like any important relationship, but at the root is trust and effective alignment mechanisms.

Leadership is stewardship, not ownership

The easiest co-CEO relationship would be static: You run your areas. I run mine. We stay where we are comfortable and avoid disrupting each other.

Over time, I think that would make both leaders—and the company—weaker.

A great partnership should expose your blind spots, challenge your attachment to your own work and occasionally put you in a role where you are uncomfortable and learning again.

After more than 20 years, I do not think the greatest risk for a founder-led company is forgetting what made it successful. Founder mode will always be there!

The greater risk is becoming so attached to what made it successful that it stops evolving.

Sometimes the best way to protect what you have built is to let someone else challenge it.

And sometimes the best way to lead is to give up the seat you know and take the one you do not.